Literature DB >> 24742128

Short total synthesis of (-)-kainic acid.

Kentaro Oe1, Yasufumi Ohfune, Tetsuro Shinada.   

Abstract

A short total synthesis of (-)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition-cyclization reaction, which provided access to a chiral pyrroline in a highly stereoselective manner. The chiral pyrroline was converted to (-)-kainic acid via the stereoselective 1,4-reduction of the pyrroline double bond in three steps.

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Year:  2014        PMID: 24742128     DOI: 10.1021/ol5009526

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones.

Authors:  Jeonghyo Lee; Sibin Wang; Miranda Callahan; Pavel Nagorny
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

2.  Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Nathan R Cichowicz; Will Kaplan; Yaroslav Khomutnyk; Bijay Bhattarai; Zhankui Sun; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

  2 in total

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